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As we began researching a trip to the Cyclades, we continually read that the Greek islands were not especially kid-friendly. Without any other explanation, we assumed this word of caution meant that the Greek islanders and other vacationers were anti-children. I heeded the advice and started looking at trips elsewhere for a hot minute, then said “damn it! I want to go,” and we booked anyway. As it turns out, the Greek people adore kids. It’s the pesky cliff drop-offs that make the islands a little dicey for kids. Long story short: we had an absolutely fantastic time and the girls came home saying this was their favorite trip ever. If you’ve ever considered Santorini with kids, do it!

Getting to Santorini with Kids

It turns out that actually getting to the Cyclades in general can be tough. Prior to the busy travel season (June-early September), you usually have to fly to Athens, lay over several hours (if not a day), then take a ferry or a puddle-jumper to your island. None of that sounded good with little ones in tow. Traveling in late-May gave us the opportunity to take a direct flight from Venice’s Marco Polo airport to Santorini on Volotea Airlines for about $700.

Accommodations

We chose to stay in Kamari Beach. While Oia and Fira–on the western side–are the most popular Santorini towns, Kamari–on the eastern side–boasts beautiful black pebbly beaches. We stayed in a two bedroom apartment at Blue Waves Hotel. At the risk of sounding elitist, we were a little worried since it was only a 2-Star; the Booking.com reviews rated it at 9/10 stars so we took a chance. Although the apartment was extremely bare bones (and the beds were terribly hard), the amenities, proximity to the beach (about a 2-minute walk), the awesome staff, and the price made up for it. We arrived hours before our room was ready due to an early flight. The staff allowed us to drop our bags and use all the facilities–pool, sundeck, bar, changing room/bathroom–before we were officially checked-in, which made the 5-hour wait comfortable. Everyone was shockingly good with kids, right down to the bartender. When Harper, the 2-year-old, got upset for any reason by the pool, he popped up a batch of popcorn for her and asked us all back to watch him make mojitos and Greek salads.

Food

I think one of the highlights of the trip was dining out. I mean that’s kind of a “duh” statement because Greek food is so amazing, but we generally dread eating out with Zoey and Harper. They act like most kids in a restaurant but we have (probably unrealistic) high expectations. Most of the restaurateurs we visited either had their own kids on-site and carted out toys if my daughters got restless, or the waitstaff did something fun with their food…little plastic monkeys stuck into the gelato, cool food picks in the shape of flags or fireworks, surprise finger-foods delivered to the table. Captain’s Corner Taverna, which was maybe two meters from the hotel, was good enough to revisit throughout our trip. Tomato croquettes, Greek salads, fresh seafood, baklava…we loved everything that came out of the kitchen. If you happen to be traveling to Santorini with kids, no matter where you stay, I highly recommend a trip over to this taverna.

Directly on the beach, Captain Hook Bar became our breakfast haunt for the holiday. Between the name and the kitschy life-size pirate statues, Zoey picked the place the first morning we were on the island. I was less enthusiastic about it based upon the decor but figured one bad meal wouldn’t kill me. Turns out the place was awesome. I think both girls ate chocolate chip crepes every morning with freshly-squeezed orange juice. Eddie and I wound up starting the day with a glass of wine and Greek coffee (think Turkish coffee but in Greece) in addition to all kinds of authentic Greek breakfast foods. Reviews on TripAdvisor are really mixed but I have to say that breakfast was pretty tasty.

Tours

Seeing and photographing the blue-roofed buildings in Oia was a lifetime bucket-list kind of thing for me. So we didn’t spend a lot of time looking around for the most beautiful, iconic spots, we decided to book a half-day private tour with Santorini Day Tours via Viator.com. Our guide picked us up outside the hotel in a van, listened to our list of must-sees, and helped us create a 5-hour itinerary to include Oia, the Profit Ilias Monastery, a quaint mom-and-pop tapas-style restaurant, and Venetsanos Winery overlooking the Caldera. Unfortunately Akrotiri had to be culled from the list due to time. The guide was patient with the girls, even helping us keep an eye on Zoey when Eddie was taking a picture and I was changing a potty training accident (ah, traveling with a potty training toddler). He also helped us time our tour so that we would be seated at a winery with glasses of wine in-hand for sunset over the Caldera.

On our third full day, we booked van service and traveled over to Fira on our own. Although the more popular way to travel from Fira town to Old Port is by donkey, we opted to ride the gondola. Honestly, unless you just love gondolas (or donkey rides), I would highly suggested saving your money and skipping Old Port. There’s really nothing down there; although, we did get a few knockout photos like the boats inside the alcove just below.

Leather sandals were on my souvenir list, and despite them being a common Greek souvenir item, they were a little hard to find. It was Fira where I finally ran across the cobbler in the image below. He and his granddaughter were fabulous. She spoke fluent English and helped me find sizes, pick colors, and tie the laces up the right way. He called Zoey and Harper over to his workbench and made them custom gold leather bracelets all while grooving to James Brown on the radio. I left with a great pair of sandals for the equivalent of $35 and the cobbler gave us all bracelets completely gratis.

Day four was bittersweet. We were tired and ready for our soft beds at home, but none of us wanted to leave Santorini. In fact, I don’t think anyone on the island wanted to leave. Our flight over to the island was packed; our flight back to Italy was half-full, if even that. Zoey, who hates everything right now (I dread puberty and those hormones), proclaimed Santorini her favorite vacation spot so far and begged to come back. I joked that we left home with little girls and were returning with tiny goddesses. The Cyclades just seeped into our blood.

A Note on Getting Around

Santorini is a small island but is much too large and mountainous to travel on foot. Taxis are surprisingly few. I read that there are only 36 cabs to be found on the whole island. Buses are said to be hot and inconsistent. Cars, mopeds, and motorcycles can be rented cheaply in all parts of Santorini, with kids, however, you have to worry about safety (car seats, etc). Save yourself the headache and book van service. Service to and from the airport ran about $20 each way. Service from Kamari to Fira rang in at about $10, I believe. The vans were pleasantly cool, safe, and efficient. Our hotel did all the van booking for us, which was an excellent service.

Final Verdict

Santorini with kids…just do it! If price is a concern, go slightly off-season like we did. Accommodations and airfare set us back around $1000. Food, tours, wine, souvenirs, shuttles, and tips set us back another $1000, but you could significantly cut that amount down by cooking for yourself inside a hotel kitchenette and cutting out wine. In terms of time, four days was plenty to see what we wanted. With a week or two, you could easily navigate by ferry among the islands and experience several. If the Cyclades aren’t on your travel bucket-list, consider adding it, especially if you have small kids.